N-bromobutanimide → 4-Quinolinecarboxylic acid, 3-(bromomethyl)-2-phenyl-, methyl ester

HRID 1166271Notes

Reaction equation

HRID 1166271 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH3:21])=[O:4].[Br:22]N1C(=O)CCC1=O>CC#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH2:21][Br:22])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 230804Methyl 3-methyl-2-phenylquinoline-4-carboxylate

Product 1

HCID 104984484-Quinolinecarboxylic acid, 3-(bromomethyl)-2-phenyl-, methyl esterYield 203.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

10 g (36 mmol) of 3-methyl-2-phenyl-quinoline-4-carboxylic acid methyl ester (compound of Description 1) were dissolved in 500 ml of CH3CN; 13 g (72 mmol) of N-bromosuccinimide were added and the reaction mixture was heated to reflux. After adding 1 g (4.1 mmol) of dibenzoylperoxide; the reaction was refluxed for 24 h; then additional 4 g (22.5 mmol) of N-bromosuccinimide and 0.5 g (2.0 mmol) of dibenzoylperoxide were added and the reaction was refluxed for 4 h. The solvent was evaporated in vacuo to dryness to yield 26.1 g of crude title compound which has been used in the following reaction without further purification.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturethe reaction was refluxed for 24 h
  3. temperaturethe reaction was refluxed for 4 h
  4. customThe solvent was evaporated in vacuo to dryness

Sources & evidence

ORD record
ord-42d57b0ffbb849c79be5df80268183d4
Source dataset
uspto-grants-2003_09
Patent number
US06613770B1

Reaction notes

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